The Painter The Pirate The Promise
by theycallmemichelle
Summary: For a challenge in my GG forum I'm in! Challenge? "What If..." Topics? The Painter, the Pirate, and the Promise. Enjoy !


**Ship: Blair and Dan…which makes Dare, which makes me wonder…well, anyway, I know they will never be together in books and most unlikely in the shows, but Blair/Dan are my new favorite couple! So here's my first "What if…?" challenge fluffy oneshot of three. First one: THE PAINTER. Slightly Book based.**

They'd been friends for awhile. He always had the good, Brooklyn-edged advice when she needed it. She always treated him like a…disease. Like a rabies-infested raccoon (she had a bad experience when she was five—and when she told him about it, he told her about his frightening Ice Capades run-in when _he_ was five).

They developed a play-by-ear relationship. He liked her, she liked him, but of course neither ever showed it. She was a Manhattan princess; he was a Brooklyn bum. It just wasn't met to be. He had already had a taste of her world with Serena, the undisputed It Girl of the Upper-East Side, but she mostly lent the coveted title to her.

Chuck was playing games with her again; Nate and her relationship were hitting a rough patch, and Serena was in jail. Her other so-called friends were not being so friendly lately. She was so vulnerable, always so trusting with certain people. Eventually he was one of those people. He trusted her a little, too, he liked her bittersweet personality. Usually she was a manipulative bitch, but when push came to shove, she was a pretty sweet girl.

Today they took a walk—she hated subways, he refused limousines—in Central Park. They were silent after discussing how Serena's mother warranted her arrest. Well, they didn't talk sometimes. They preferred to text. If anyone—mainly, one of Gossip Girl's many sources—saw Lonely Boy and the Queen B actually together without looking slightly repulsed, people would talk.

So he with his Voyager and she with her enV2 walked in the same path, often purposely letting a wide tree come between them and a dog-walking couple and so on. Sometimes he bent to tie his shoe when there were no obstacles and their paths looked suspicious.

He was getting pretty hungry, and started to think about how her last name, _Waldorf_, was also a salad. Then he remembered—today was Wednesday: Chinese take-out night at the Humphrey apartment. Without Chinese take-out, he and Jenny would probably starve, their father barely cooked—but when he did, the aftermath was often puking or terrible heartburn. Or explosive diarrhea. Thank god for Tums. So he took out his cell phone—they had been silent a little whiles—and sent a little message to the queen.

**DAN: 2day = Chinese take-out nite the loft. U in?**

**BLAIR: Chinese take-out? W/you? In Brooklyn? Oh, pls. Gag me!**

He pretended to glance in her direction at the ducks in the pond, but gave a roll of his eyes that was clearly seen by her.

**BLAIR: Are you srsly asking me 2 do tht? Brooklyn is way 2 far 2 wlk…didn't bring cab $$$, and I'm pretty sure u have none.**

**DAN: Pls? I'm starving. And J is way 2 annoying on Wednesdays 4 me 2 bear!!**

**BLAIR: ?**

**DAN: its Wednesday, her "art day". She goes round loft looking 4 inspiration. Somehow the aroma of lo-mein helps. Idk.**

**BLAIR: Omg! R u using ur lil' sister artistic escapades 2 score a d8 w/me??**

**DAN: ????? No!!!**

It was a lie. In a way, he wanted to try it. Try and see what it would be like with her. Wondering if she would be like Serena, or maybe he'd be riding an entirely new roller coaster.

She knew it was a lie. As much as she might detest Brooklyn lifestyle, she didn't detest him. She was craving a new experience, and she was guessing he was too. Nate and her were going downhill. She decided not to pressure him too much.

**BLAIR: K. I'm in! Just 1 condition…**

**DAN: ?**

**BLAIR: NO SUBWAYS!**

He bit back a laugh, but not a lopsided grin. She was so high maintenance, but in a cute way.

**DAN: Lol, k. Take a wlk w/me?**

She smiled softly. He was never complicated.

**BLAIR: K.**

It was a long walk. She didn't realize how far Brooklyn was from the Upper-East Side, let alone Central Park. And by the time she reached his little apartment, walking up to the sixth floor ("I can't believe you don't even have elevators here!"), she was starving. She was craving a shot of whiskey with some muscles, but she had to settle for downtown take-out.

The apartment was surpassingly cozy. It was quaint, with a few tossed aside shirts (she didn't dare wonder if they were washed or not, fearing puke) and a guitar in the corner. Photographs lined the walls, all of some ancient rock band she knew nothing of. Lincoln Hawk? Maybe her mother would know, but then again, she was never much of a groupie back in her day—more like an Upper-East Side princess, like her daughter.

Jenny was sitting in the kitchen, staring fixedly at an empty canvas. She clasped a small take-out box inscribed with Chinese characters and a pair of chopsticks in the other. As she gazed, every so often the chopsticks would strike into the box like a venomous cobra and stick a piece of food in her mouth: Lo-mein. He knew his sister well. A pair of headphones was plugged into her ears. She bobbed her head to an inaudible beat.

"What's she doing?" She had to ask him, standing next to him on the threshold. He held his jacket over his shoulder like men do in those tuxedo commercials. But he looked more cool, casual…natural.

"I told you. It's Wednesday. Lo-Mein and Katy Perry inspire her," He simply explained, shrugging and striding over to the counter, tossing his jacket on the couch. She had no choice but to follow, catching a whiff of fragrance as she passed the couch—Wow. He wears nice cologne.

"Okay, do you want…general Gao chicken, or white rice?" He held up two boxes similar to Jenny's.

She bit her lip, contemplating, but not for long. "Definitely the rice. Chinese food is way too high in fat anyway without the spicy chicken. Rice is simple—" Like him. "And never in my life have I heard of a general named Gao," she added. He laughed—she liked his laugh.

"Good choice. And, to tell you the truth, I don't think there even is one. I like his chicken, though," He said, tossing the box at her. She barely caught it with her freshly manicured nails. "Ooh," he gasped mockingly with a smirk.

"Ooh," she echoed, grinning. "I should be the pitcher for the Yankees."

"If you can throw better than you catch," he laughed, noting her mistake.

"Right." She blushed. Funny—she never blushed around him.

"Come, my little protegee. Learn the Humphrey lifestyle," he called, sitting lazily and giving the seat by the counter a little twirl. She giggled, sitting beside him.

"'Kay, but no way am I becoming a Brooklyn Apprentice—Donald Trump scares me too much on the show already," she warned.

"Hey—we have something in common!" He pointed out brightly as he fingered two pairs of chopsticks. She laughed as he offered her a pair. "Chopsticks, milady?"

"Please, kind sir," She drawls in a fancy accent—she imitated Serena's mother—and accepts the chopsticks. Then she realized something as she held the chopsticks dumbly in her hand. "I don't know how to use chopsticks."

"Don't feel bad. I didn't learn until I was, like, twelve. It goes like this," He showed her how to handle the chopsticks step-by-step.

She failed. "Hard to believe the queen of Constance Billiard can't do something that the Lonely Boy from Brooklyn can," she made up for it by insulting him. There she went again.

"I am going to ignore that and show you how to use chopsticks if it's the last thing I do. Hmm…" He thought for a moment. "Bad choice for the rest of my life." Subtly burning her? Wow, he was good. She laughed anyway.

"I still can't do it," she sighed as he showed her for the third time.

"Here," he took her hand and arranged the chopsticks in her fingers. His touch lingered for a second too long. He withdrew his hand instantly. "Sorry."

"It's okay," She whispered.

"What?" His head whipped around to face her. She stared at her rice.

"I said: it's okay." She repeated, a blush rising to her cheeks. She took a bite of rice to cover it up.

"What, no insult or talk-back? You must be in a really good mood today." He laughed. "Hey, look! You're doing it," he pointed out as she took another mouthful of the Chinese rice.

"And so the student becomes the teacher," she said, snapping her chopsticks at him defiantly and eating more rice. It was a pretty good feeling. She didn't just mean the chopsticks or eating.

"Ah, but she's cocky," He observed, taking a bite of chicken. "Damn, this is good. I mean, sometimes the Chinese joint we buy from has their off days, but today is a good day," he relished the taste.

"Is that so?" She found his taste-savoring amusing.

"Hey, did I ever tell you about the time we found a cockroach in our scallion pancakes? It was so gross, missing its head but still crawling, my sister screamed so loud..."

She liked him. That was all there was to it.

It was about two weeks later. Prom was coming up. Chuck was out of her system, supposedly. Nate wanted her to move in with him. That hurt him in the gut. To think that her, his Queen B (but she was only his secretly, in his head) might end up cooped in an apartment with someone else. They may have been dating, and Nate was a good guy, but she was too good for it all. She deserved much more. Besides, he could tell Nate was only afraid of her straying towards Chuck—it was more like the opposite. She was straying to him. He was actually one of Nate's best friends, and she was straying to him. If he would pause from worrying about Chuck, he would realize that.

Luckily, Nate wasn't that smart.

They had gotten over the almost-hand-holding incident and moved on. Her prom night was going to be perfect, she looked so happy, texting about it time and time again. He loved her smile, he noticed one day. It was genuine and a treat—it was rare to see it replace her sour, regal expression. It was even brighter when she laughed.

It didn't take long to realize that he was falling in love with her. They say that gentleman prefer blondes—well, that must mean he wasn't a gentleman, because he preferred a certain brunette.

It was Wednesday. They had taken a walk. They made it back to his place again. She had already opened the rice, he with his chicken, and Jenny was nowhere to be found.

He had a surprise for her.

"Humphrey, I don't feel very comfortable in a dingy Brooklyn apartment with a surprise waiting for me. Oh, no—!" She was saying, but she paused to widen her eyes. He grew concerned for a second. But only a second. "You didn't buy me a cabbage patch kid, did you? Well, if you did, just know that she is not going to be doing Cedric on a regular basis. Just so you know."

He burst out laughing. "Trust me—any cabbage patch of yours isn't going anywhere near mine. The Manhattan measles will wipe out his Brooklyn edge entirely!"

"Very funny," she drawled sarcastically, rolling her eyes.

"Follow," he grunted through a mouthful of chicken and lead her to Jenny's room. Jenny was sitting on her bed; already half-done with her crab ragoons and bobbing her head to what sounded like the Black Eyed Peas. She startled when she saw the Queen enter her room. She tore her Hello Kitty headphones (even at fifteen they still fit her) off immediately, not bothering to shut off her iPod. "Hi, Blair!" she squeaked, smoothing her skirt out and grinning. He saw a piece of crab sticking out of her front tooth. The girl next to her opened her mouth to point it out, but he elbowed her subtly to shut her up.

"Hello, Jenny," she instead greeted warmly—with a tinge of faux.

"Dan, did you…?" Jenny began to ask him, her voice trailing off and her wandering eyes landing on the thing covered by a bed-sheet. It resembled a canvas. He nodded, glanced at the queen, and led her over to the canvas by the window. Sunlight poured in, giving it a subtle glow, like it was at an art show or something. Jenny hovered closely behind.

"Blair, this is what Jenny was working on the Wednesday before last. Remember?" He began, standing next to the canvas while she stared fixedly at it, puzzled.

"Yeah…but it was blank," she pointed out, remembering.

"Not anymore!" Jenny giggled, startling her. He shot a small glare at his little sister, whose smile evaporated and she withdrew back to her bed, plugging in her headphones again but still watching intently at the unveiling of her masterpiece.

"Blair Waldorf, I humbly present to you the first model-inspired masterpiece of critically acclaimed Brooklyn artist Jennifer Humphrey!" He said in a faux art-dealer accent. Then, with a touch of hesitant suspense, he tore the bed sheet from the canvas (almost knocked it over) and revealed the painting.

She was expressionless at first; he was worried that she didn't like the painting: it was from that Wednesday, when he taught her chopsticks. He and her were sitting at the table, with their Asian cuisine, and he was doing just that: teaching her how to use the impossible art of chopsticks. They both had an silly grin on their face, as if they had just been laughing unstoppably. He was holding her hand to steady her chopsticks, and she was fumbling. The painting was in movement, but two-dimensional. It was amazing. Jenny had even made their mediocre apartment look first class.

"Wow," she gasped. "It's…beautiful. Jenny, you are…incredible," she turned to the artist. Jenny was beaming, basking in the praise of the queen B.

"It was inspired by you guys," she modestly insisted, but he could tell she was dancing inside.

"It really is gorgeous, Jen." he repeated himself for the fourth time since he saw the painting that morning.

"What's it called?" the queen asked Jenny.

"Read the bottom," The painter instructed, nodding to the colorful canvas.

He and the queen both leaned forward, squinting at the inscription.

_Chopsticks._


End file.
